The author explores the feminine/masculine binary and what is meant by being “in” this binary versus “of” it. He considers Freud’s views on female “otherness” in light of today’s changing theories and practices regarding sexuality and gender. Newer ideas are seen to supplement rather than replace traditional ones; it is noted that binary dichotomies remain present in each individual’s psyche but can yield to more complex and nuanced ways of thinking about gender differences. Concepts such as primary femininity, core gender identity, binary logic, male primordial vulnerability, and gender fluidity are discussed, along with their implications for psychoanalytic thinking and practice. In particular, the male analyst’s psychic bisexuality or bigenderality – including the “feminine” interior within every male born of a woman – is examined as it relates to his clinical functioning and efficacy. Finally, a brief clinical vignette is presented to illustrate some of these points.